The VP, Operations is the most senior leader in the Operations function and a peer member of Riipen’s executive team. This role owns the architecture and performance integrity of Riipen’s Operating System so the company can scale revenue growth, margin, and outcome reliability in parallel.The VP, Operations builds the systems that turn ambition into predictable execution. They ensure that growth compounds rather than fragments, that commitments remain credible, and that impact scales without sacrificing quality or sustainability.When this role is working well, Riipen runs with clarity. Decisions are made once and enforced consistently. Leading indicators surface early. Escalation is predictable. Teams move fast because the system is strong.This role partners directly with the CEO to institutionalize disciplined execution across the company.Key Responsibilities Operating System Architecture and Executive Cadence Own the full scope of Riipen’s Operating System architecture, including enterprise OKRs, KPIs, scorecards, decision forums, accountability structures, and company-wide operating rhythms.Design and maintain the executive cadence that translates strategy into measurable execution across Product, Revenue, Delivery, Employer, and Finance.Ensure cross-functional planning is disciplined, time-bound, and aligned to enterprise priorities.Maintain clarity of decision rights, forum ownership, and escalation paths.Functional leaders retain ownership of their strategic domains and targets, and the VP Operations ensures those commitments are governed, measured, and executed through Riipen’s Operating System.Enforcement, Gates, and Enterprise Discipline Enforce Product-defined quality gates and outcome reliability thresholdsEnforce Finance-defined sustainability gates, including margin discipline and unit economics.Ensure adherence to decisions made across the business through functional forums (Product, Revenue, Strategic Initiatives, and Finance)Exercise authority to pause launches, reduce scope,



or block commitments that violate agreed gates or create unsustainable risk.The VP, Operations role is not a facilitator of activity in the business - they are critical in sustaining and reinforcing the architecture that will help Riipen to grow.Launch and Scale Governance Own the system to monitor operational readiness gates for new products, delivery models, employer programs, and geographic expansion.Ensure launches occur only when quality, sustainability, and execution standards are met.Protect enterprise capacity by preventing initiative overload and reinforcing start-stop discipline alongside Strategic Initiatives.Growth should increase strength, not fragility.Performance Integrity, and Signal Design Build leading indicator systems that surface operational deterioration early across revenue, delivery, quality, and marginReduce operational variance and late-stage surprises through disciplined execution frameworks.Own the CRM as the enterprise system of record, including schema governance, data integrity, access controls, and enforcement signals.Ensure workflows reinforce operating standards.Partner with Revenue Operations, which owns revenue workflows within the CRM, while maintaining enterprise governance authority.Executive Leadership and Board Partnership Serve as a peer executive responsible for enterprise execution clarity and disciplineProvide board-ready reporting on operational health, leading indicators, systemic bottlenecks,



and execution risk.Partner closely with the CEO to ensure strategic ambition is matched with operational integrity.Support executive hiring and onboarding for operationally critical roles.Areas of Oversight Revenue Operations including Director of Operations as a direct reportData and Operations team with four indirect reportsCompliance function with one direct and one indirect reportLegal oversight related to governance, escalation, and enforcement rather than direct legal executionSkills, Knowledge and Expertise These aren’t hard requirements, but will be indicators that guide our search.You may be a good fit if you:Bring 10+ years of leading operations, business systems, or strategy in a scaling Saa S or technology organization, with direct responsibility for company‑wide operating rhythms and governance.Have a proven record of building or transforming operating systems that drive disciplined execution, cross-functional alignment, and measurable business performance.Are fluent in enterprise operating frameworks - OKRs, KPIs, governance forums, and know how to use them to turn strategy into predictable outcomes.Demonstrate credibility in enforcing standards and decision integrity across functions while still enabling collaboration and growth.Combine systems-level thinking with a strong command of data models, CRM architecture, and operational health indicators.Thrive in ambiguity, quickly building structure and rhythm where none exists, and scaling those systems sustainably as the business grows.Partner effectively with executive peers and boards, communicating complex operational signals in clear, decision-ready formats.Lead with conviction and curiosity—balancing attention to detail with awareness of enterprise priorities and long-term resilience.Value a transparent, inclusive, and feedback-oriented culture and believe robust architectures empower people, not constrain them.We believe that diverse teams are high-performing teams and we strive to employ individuals with a diversity of backgrounds, experiences, and perspectives.Benefits Remote/travel working opportunities (when appropriate)4-weeks of annual vacationExtended Health and Dental benefits from your first dayFlexible health spending

📌 Vp, Operations (Canada Or Us Remote) (Winnipeg)
🏢 Talantir
📍 Winnipeg